1-(bis(2-hydroxypropyl)nitriloethylene)-5-stiba-1-aza-4,6-dioxacyclooctyl antimony-ether

ABSTRACT

A WOOD PRESERVATIVE COMPOSITION COMPRISED OF CREOSOTE IN WHICH IS DISSOLVED THE NOVEL ANTIMONY CONTAINING COMPOUND 1-(BIS(2-HYDROXYPROPYL)NITRILOETHYLENE)-5-STIBA-1AZA-4,6-DIOXACYCLOOCTYL SB-ETHER WHOSE STRUCTURE IS   BIS(1-((HO-CH(-CH3)-CH2-)2-N-(CH2)2-),3,7-DI(H3C-)-1-AZA-   5-STIBA-4,6-DIOXACYCLOOCT-5-YL)-

United iii- 1 tiliairn ABSTCT OF THE DISGLOSURE A wood preservativecomposition comprised of creosote in which is dissolved the novel antiony containing compound1-(bis(Z-hydroxypropyl)nitriloethylene)-5-stibaaza-4,6-dioxacyclooctylSb-ether whose structure is This is a division of application Ser. No.221,082, filed Ian. 26, 1972 now Pat. No. 3,764,378.

FIELD OF THE INVENTION This invention relates generally to a woodpreservative composition, and in particular to an organic antimonycompound thatis soluble in creosote to provide a composition for thetreating of wo'od.' I m I There has now been discovered, a novelantimony Olfganic compound which is soluble in creosote and can be usedfor enhancing the properties of the creosote, i,e.,. for rendering morefire retardant the creosote which is to be used for the impregnation ofwood.

BACKGROUND on THE mvnirrron Because of its toxic properties, creosote iswidely used as a wood preservative. Creosote is a distillate of the coaltar that has been produced by the high temperature can bonization ofcoal; the distillate begins at about 200 C. and has a continuous boilingrange of at least 125" C. It is comprised of liquid and solid aromatichydrocarbons and contains appreciable quantities of tar acids and tarbases. Thus, creosote is not a single chemical substance but is amixture containing a great number of aromatic compounds. When the,creosote is impregnated into wood, it renders the wood toxic to fungiand most organisms.

It is desirable for many purposes that wood be not only rot resistantbut fire resistant as well. Antimony trioxide has the property offlameproofing canvas. Antimony tri oxide is also used in paints,lacquers, porcelain enamels, glass, and adhesive cements. As a whitepigment, the bid ing power of antimony trioxide is somewhat greater thanthat of lithopone. It is also used in conjunction with tita niurndioxide to improve suspension properties and prevent chalking. DuringWorld War II, approximately one-third of the total consumption ofantimony in allforms was for the treatment of canvas. The canvas orother material to be flameproofed is dipped in a compound containinganti mony trioxide, chlorinated parafiin, and possibly otherconstituents, such as paint pigments; and the resultant canvas isfiame-resistant and will not support combustion in the absence of asourceof external heat.

While the dip coating" of a. thin material such as canvas is sufficientto protect the material, a simple coating is not sufficient to protectwooden beams or logs. The wood must ,sizzstrz SUMMARY OF THE INVENTIONThis invention relates generally to wood treating come positions andmore particularly to a solution of 1-(bis(2hydroxypropyl)nitriloethylene)-5-stibal-aza 4,6 dioxacyclooctyl Sb-etherin creosote. This novel organic antimony compound has the generalstructure v on on. F CHPAIHMGHQ oH=-011-0 N-CHr-CHr-N Sb--0 I 011-4311-4311; cu=--on-o E (5H3 i The novel antimony compound is formed bythe reac tion of antimony oxide (Sb O with N,N,N',N'-tetrakis-(Z-hydroxypropyl) ethylene diamine.

The N,N,N',N'-tetrakis(Z-hydroxypropyl) ethylene diamine is readilyavailable commercially as a viscous, water-white liquid. The antimonytrioxide is commercially available as a white to buff colored solidpowder.

The novel organic antimony compound is soluble in creosote. To obtainthe wood treating solution, the organic antimony compound may either beformed separately and added to the creosote or may be formed in situ inthe creosote. Forming the organic antimony compound in situ isadvantageous when the solution of the organic antimony compoundinc'reosote is to be used for the impregnation of .wood because it thenis not necessary to purify the product. The solution of the organicantimony compound in creosote may be used in the conventional manner aswe e sweete -fai t imr ssn t n f-ww 'llflie'wood.rrialiydie impregnatedwith asciption otthe organic antimony compound. in. creosote by eitherthe well known fempty. cell or -f ull c el l f ,method to par-nundesired retention o' f,.the preservative in the .wood. As with creosote;the amount of preseryative solution of this m vention to be placed. inthe, wood will vary with the use to whichthe wood is to be placed. Forexample, 4 to 5 pounds of the preservative solution would be retained inthe wood per cubic foot of wood when the wood is to be used, forexample, for fence posts. For lighting poles, rail= road 'lies, and thelike, the retention, of course, increases to 5 to 12 pounds of thepreservative solution per cubic foot of wood.

The organic antimony compound of this invention, the

solute, can be used to the extent of forming a saturated solution in thesolvent creosote. Normally, a 34% by weight of organic antimony compoundin the creosote solution is considered sufiicient to provide theadditional tire retardance to the wood.

DETAILED DESCRIPTION The invention will be illustrated more clearly bythe following examples.

Example I Two hundred sixty five grams of N,N,N',N-tetrakis(2-hydroxypropyhethylene diamine is charged to a 1 literstirrer flaskequipped with a watertrap. Fifty grams of xy-= lene is added, themixture; heated to .125 .C. and then 315 grains of antimony trioxideadded over aperiod of 5 minutes. flhetmixture is refluxed for 1 /2 hoursat 107- 1'23. Ciandth'e water evolved from the compound fOlfl'iEt tioniscollected in the trap. The viscous product mixture is cooled to roomtemperature and this new composition Patented July 2, 1974 of matter ispurified lay acetone extraction. The purified compound is pale yellowsolid.

Based on a molecular weight of 840, an elemental anti mony content of29.0 (theory 289) and Sb-O band at 16.9 microns, and NMR analysis, thestructural formula of'the compound is The solubility if the compound increosote to the extent of about 30 grams of compound per 100- grams ofcreosote at room temperature.

Example II To 10,000 grams of creosote was added 265 grams of N,N .il,l-I'--tetrakis (2-hydroxypropyl ethylene dianiine). The mixture'isplaced in a stirrer, -1'eactor andheated to 125 C.; then a 315 gramsof'antin ony trioxideis added trioxide is not. However, disappearance ofthe solids as the reaction proceeds permits the o rater to determinecorn Ii I plction of the organic reaction as the novel antimony compoundof the invention is formed.

The foregoing has described a novel organic antimony compound which canbe used With creosote for the treatment of wood. Treating solution canbe formed by the organic antimony compound either being synthesized andthen added to the cresote, or the compound being made in situ in acreosote medium. The novel treating solution. can he used inconventional equipment for the impregna tion of WOOd.

What is claimed is:

it. The compound represented by the structure g cm DANIEL E. WYMAti,Primary IExarriincr I A. Pr DEIVIERS, Assistant Examiner C1. Ji l-L21-4; I06--l5 FP; 117 147, 151'; 424M296, 339, 34s:

